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    A Hot Dog Mogul Is Serving Up This Oceanfront Florida Penthouse for $32.5 Million

    Totally bummed you can’t swoop in and grab America’s most expensive home that just hit the market in Southwest Florida with an eye-popping $295 million price tag? Now’s your chance to snap up the next best Naples thing, and it’s currently up for sale. But you’ll still need almost $33 million to pick up the keys to the freshly remodeled penthouse, which would set a record for the priciest resale unit in the affluent area if the place goes for anywhere near that amount.

    Property deeds show the residence was last sold in fall 2022 for $11 million. Dick Portillo—the Chicago-born founder of the Portillo’s restaurant chain, best known for its Chicago-style hot dogs and Italian beef sandwiches—subsequently embarked upon an extensive renovation of the 2002-built premises in collaboration with an investment team consisting of C&E Builders and Theory Design’s Ruta Menaghlazi. The listing is held by The Earls | Lappin Team of John R. Wood Christie’s International Real Estate.

    The spacious living room is flanked by a fireside lounge area.

    Naples Kenny Photography

    Resting on the 20th floor of The Seasons at Naples Cay—a gated beachfront high-rise building bordering Park Shore to the south and Pelican Bay to the north—the revamped abode offers five bedrooms and seven baths in almost 12,000 square feet of living space boasting herringbone oak floors, high ceilings and designer lighting throughout. Floor-to-ceiling walls of glass and 4,800-plus square feet of outdoor terraces also offer up panoramic vistas stretching from the Gulf of Mexico and Outer Clam Bay to the city lights of Naples.

    Highlights include an elevator-accessible foyer leading to an open-plan great room holding a fireside living room and dining area, along with a gourmet kitchen sporting champagne eucalyptus cabinetry, white Macaubas quartzite countertops, an expansive eat-in island, top-tier Miele appliances and an accompanying breakfast nook flanked by a family room. A secluded master wing features a water vapor fireplace, wraparound balcony with a spa, separate morning lounge, sauna-equipped fitness studio, and dual dressing rooms and baths.

    The ocean-view terraces come complete with an outdoor kitchen and spa surrounded by a “living” wall.

    Naples Kenny Photography

    Elsewhere are four additional en-suite bedrooms, including one with its own kitchen and living area, along with glitzy amenities ranging from a backlit onyx entertainment bar and glass-encased wine vault to a handsome study warmed by a fireplace; and topping it all off are plenty of community amenities—courtesy of a hefty $11,563 monthly HOA charge—which include a guard-gated entry, 24-hour doorman, swimming pool, fitness center and billiards room.

    A self-made billionaire and longtime real estate investor, Portillo also maintains an additional Naples condo and has renovated several properties in the Chicago area.

    Click here for more photos of Dick Portillo’s Florida penthouse.

    Naples Kenny Photography More

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    ‘The Good Place’ Star Jameela Jamil Seeks $7.2 Million for Her Hollywood Hills Mansion

    Scarcely one year ago, Hollywood actress Jameela Jamil and her longtime partner James Blake dropped an impressive $6.4 million to buy a hulking mansion sited atop L.A.’s famed Mulholland Drive, directly overlooking the entirety of Hollywood.

    The English couple—she famous for her roles in films and TV show projects such as “The Good Place,” “She-Hulk: Attorney at Law,” and most recently, “Pitch Perfect: Bumper in Berlin,” he a Grammy-winning musician—are already moving on from their still-relatively-new Hollywood Hills home, having flipped the place back up for sale with a $7.2 million ask. Rick Ojeda of Carolwood Estates holds the listing.

    Clinging precariously to the side of a nearly sheer cliff, the house appears to be a relatively humble, single-story structure from the street, but it drops down mullet-style to four full levels out back, encompassing a nearly 7,000 square feet of mansion-sized living space. There are a total five bedrooms and 6.5 bathrooms on tap, per tax records.

    Built in the late ’80s and styled as a Mediterranean-style villa, the hillside home was recently given a contemporary renovation.

    Google Earth

    Originally built in 1989, the home’s dated architecture was given a thorough contemporary makeover by Dalinger Designs just prior to Jamil and Blake’s purchase. Today, the hillside structure is described in the listing as “Villa de Vistas, an extraordinary Contemporary Mediterranean compound … with an earthy flair.” And indeed, the home’s views are unquestionably extraordinary, with walls of glass spanning the entire back of the residence and framing unstoppable vistas of nearby canyons and distant city lights.

    A convenient elevator ferries residents and guests throughout all four of the home’s level. The front door opens into a vast main living area with a wood-paneled kitchen—naturally complete with commercial-grade stainless appliances—and an adjoining fireplace-equipped living room and indoor/outdoor living space. Just below that, a 2,000-square-foot master retreat is loaded with amenities, boasting a fireplace, lounge area, spa-style bathroom and a walk-in closet bigger than many studio apartments.

    Below the master are various guest bedrooms, all of them equipped with ensuite full bathrooms. The home’s lowest level is recreation-themed, sporting a movie theater, gym and a wellness center with a sauna. Out back, a pool and spa overlook the aforementioned views. Other amenities include state-of-the-art home automation and surveillance systems, plus a three-car garage and a lounge space that could be converted into a recording studio, per the listing.

    In addition to their for-sale Hollywood Hills manor, Jamil and Blake also own a spacious second home in Georgia, down in the Atlanta suburb of Fayetteville. More

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    Richard Perry and Jane Fonda’s Onetime Beverly Hills House Can Be Yours for $11 Million

    Jane Fonda once said she knew this tasteful Beverly Hills beauty was a house where she could live very happily as soon as she and Richard Perry drove through the gate for the very first time. The couple went on to pay late film and TV director John Rich $7.3 million for the place in summer 2012, and Fonda even held a party there to celebrate her 75th birthday.

    But life happens. After eight years together, the Oscar-winning actress and her music-producer partner wound up splitting and putting the home up for sale in January 2017 for a little less than $13 million. Finally purchased a year later by an unnamed Irish celebrity for a substantially reduced $8.5 million, and leased out in the years since, the modern residence in the Trousdale Estates neighborhood has now returned to the market, this time asking a speck under $11 million.

    An inviting living room is centered around a stacked-stone fireplace.

    Jeremy Spann

    Built in the early 1960s, and subsequently updated, the two-story structure is fronted by a gated motorcourt flanked by an attached three-car garage. Tucked away on almost an acre of land overlooking ocean and mountain vistas, the four-bedroom, six-bath abode features a little more than 7,100 square feet of open-concept living space boasting bamboo floors, vaulted ceilings and double-glazed walls of glass providing seamless indoor/outdoor environs.

    The many highlights include an entry foyer displaying a staircase and glass-encased elevator, plus a window-lined great room anchored by a dining area and sunken living room equipped with a stacked-stone fireplace stretching to the ceiling and an adjacent wet bar. A family room sits next to the gourmet kitchen, which is outfitted with an eat-in island, verde quartz countertops, high-end Miele and Wolf appliances, and a breakfast room with sliding glass doors leading out to an al fresco dining terrace.

    A meditation garden sporting a fountain is the ideal place to relax.

    Jeremy Spann

    A fireside master retreat on the main level is spotlighted by a separate sitting area and an office space, as well as dual walk-in closets and luxe baths; and the lower level holds a gym, a seated bar, lounge area and screening room clad with cork floors. The amenities continue out to the tree-laced grounds, which host numerous patios, a solar-heated swimming pool surrounded by a sundeck, fire-pit and serene meditation garden bolstered by a fountain.

    The listing is shared by Jonathan Nash of Carolwood Estates and Tyrone McKillen of Official.

    Click here for more photos of Richard Perry and Jane Fonda’s former Beverly Hill house.

    Jeremy Spann More

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    Music Titan Irving Azoff Just Dropped $11 Million on the Beverly Hills Estate Next Door

    Music mega-mogul Irving Azoff and his longtime wife Shelli are apparently feeling very crowded in their neck of the Beverly Hills woods. Two years ago, the pair plunked down an impressive $21.5 million on the house immediately next door to their longtime 90210 estate, which they’ve owned since 1985. The couple are in the process of demolishing that recently acquired house and combining the property with their main residence.

    But a 3.2-acre slice of Beverly Hills just isn’t quite enough breathing room. Records show the Azoffs have now paid an additional $11.6 million to buy yet another house, this one a half-acre estate immediately adjacent to the other two properties they own.

    Back in 2013, the Azoffs moved out of their longtime Beverly Hills home and subsequently demolished the existing structure. They’re recently completed the construction of an all-new, ultra-contemporary residence, a decade-long project reportedly plagued by delays and cost overruns. (Back in 2015, the Azoffs headed to arbitration to resolve a financial dispute with Malibu-based architect Scott Mitchell, whom they had hired to oversee their new home’s creation. A court judgment subsequently awarded them more than $2.1 million.)

    As for the Azoffs’ new real estate acquisition, the half-acre estate includes a 7,200-square-foot mansion built circa 1926, per tax records. The red tile-roofed, Spanish Colonial-style structure was recently renovated and includes a mixture of hardwood floors and carpeting, numerous sets of French doors and an updated kitchen with a bulky center island and commercial-grade stainless appliances.

    Although it seems likely that the Azoffs may opt to demolish the house, the current structure also would make a sumptuous guesthouse or lavish staff quarters, with five bedrooms and seven bathrooms on tap. The lushly landscaped property also offers an outdoor fireplace, large swaths of grassy lawn, a rectangular swimming pool and even a full-size tennis court.

    The giant Azoff estate now spans nearly four acres and includes three large houses, at least one of which is slated for demolition.

    Google Earth

    With the addition of this new property to the Azoffs’ already grand estate, their as-yet-unfinished new compound has swollen to nearly 4-acres of land in one of the best pockets of Beverly Hills. Directly across the street is Ari Emanuel’s $28 million estate, and only one block away is the $165 million main residence of Jeff Bezos and Lauren Sanchez.

    Azoff, who is frequently described as the most powerful man in the music industry, maintains an impressive stable of other homes, including a Malibu property and a 17,000-square-foot contemporary vacation mansion in La Quinta’s guard-gated Madison Club. More

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    A Late Real Estate Titan’s 50-Acre Wyoming Ranch Sells to Prominent Virginia Family

    When Thomas E. “Teddy” Gottwald heard that a sprawling Wyoming guest ranch long owned by the late real estate mogul Gerald (Jerry) T. Halpin and his wife Helen had just hit the market for the first time in over five decades, it tugged at his heartstrings. After all, he and three generations of his close-knit family began vacationing at Lost Creek Ranch in the mid-1990s, and it has since become one of their favorite spots.

    The president, CEO and chairman of Virginia-based NewMarket Corp.—a global developer and manufacturer of fuel and oil additives—went on to acquire the spread, which was originally listed for $39.95 million last summer. His plans? To honor the property’s legacy by using it as a family retreat for blocks of time each year, while also continuing to welcome visitors.

    “We have enormous respect for the Halpins, their stewardship of the land and commitment to the Greater Jackson Hole area, and their creation of the premier western guest ranch that is Lost Creek,” states a letter introducing the family on the ranch website. “We plan to build on this and look forward to continuing this nearly 100-year-old tradition at Lost Creek, introducing others to the West, and giving more guests the same experience that helped shape who we are.”

    Lost Creek Ranch is bordered by the Grand Teton National Park and Bridger-Teton National Forest.

    Latham Jenkins/Live Water Properties

    Gottwald’s purchase gains him a 50-acre expanse of land resting amid the foothills of the Gros Ventre Mountains, about 30 minutes from downtown Jackson, that contains more than 25 structures paired with a large roster of recreational pursuits—all if it surrounded by protected federal land offering sweeping views of the Teton Range in Grand Teton National Park to the west and Bridger-Teton National Forest to the east.

    Originally purchased from San Francisco financier Albert Schwabacher by the Halpins and their partners Karl and Tina Weber back in the late 1960s, the Halpins became sole owners of the tract in the late ’80s. Through the years, the couple donated 50 of the site’s original 120 acres to the aforementioned park and placed another 20 acres under a conservation easement that prevents development, with the remaining 50 acres holding a main lodge and multiple rustic log cabins.

    Other highlights include a spa with fitness facilities, as well as a swimming pool, boat and well houses, a barn, large corral and access to outdoor activities ranging from horseback riding to scenic rafting trips down the Snake River. 

    Recreational activities at the 50-acre ranch include horseback riding and scenic rafting trips down the Snake River.

    Latham Jenkins/Live Water Properties

    Best known as the first real estate developer to build in Virginia’s Tysons Corner community, just outside of Washington, D.C., Jerry Halpin died in August 2017 at age 94. Helen, his wife of 67 years, passed away almost a year later in 2018. They are both buried on the ranch. As for Gottwald—whose family ranks as one of the richest in the nation, with a $3.1 billion net worth—he and his wife Ann Parker Gottwald maintain a boutique inn called The Georges in the Virginia city of Lexington. They’ve also owned a ranch in Montana for almost 20 years.

    The listing was held by Latham Jenkins of Live Water Properties; Carlos Ordoñez of Hall and Hall repped the buyer

    Click here for more photos of Teddy Gottwald’s Wyoming ranch.

    Latham Jenkins/Live Water Properties More

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    A Private Equity Billionaire Paid a Record-Breaking $44 Million for This San Diego Home

    Back in October, an oceanfront Del Mar house sold for a whopping $44.1 million, sending shockwaves through the quietly posh Southern California beach town and setting a new record for the most expensive San Diego County home ever sold. The out-of-left-field, off-market transaction came even as the San Diego real estate market has effectively stalled over the past year, with the deal pipeline choked by high interest rates, recession fears and low inventory. And the transfer also eclipsed Bill Gates’ recent $43 million purchase of an arguably more impressive house on the same strip of sand.

    Property records indicate the $44 million house was purchased by a mysterious Delaware-based LLC, a common business tool used by the wealthy to cover their real estate tracks. But it’s certainly worth noting that the mysterious entity is managed by a longtime associate of Egon Durban—the high-flying, billionaire Silicon Valley dealmaker who has a known affinity for both record-breaking transactions and high-end real estate. Durban, the co-CEO of private equity giant Silver Lake, sports a personal net worth that tops $1.5 billion, according to Forbes.

    Built circa 1940s, the ranch-style compound includes three separate buildings and parking for 20+ cars.

    Google Earth

    Since the house was never on the market, photos are virtually nonexistent and details are few. But certainly the vast majority of its value lies in its oceanfront location—the property spans just over an acre of flat land, right on the sand—rather than the structures themselves. The main residence is unremarkable, large and well-maintained but visually dated. The property was built decades ago by prominent Hollywood real estate developer C.E. Toberman, founder of Grauman’s Chinese Theatre and the Hollywood Bowl, and remained in the extended Toberman family until Durban’s purchase.

    In addition to the U-shaped main house, which is single-story and painted a deep navy blue, there are two ancillary buildings on the property. Each of those includes a two-car garage and additional living space, likely for guests or live-in staff. The oceanfront compound also boasts a full-size tennis court—a very rare thing on the shores of Del Mar—and a gated, blacktopped driveway with off-street parking for dozens of cars. There’s also an outdoor swimming pool, plus a sizable backyard with a grassy lawn and a wooden deck with stairs descending to the sandy beach. Altogether, the estate sports eight bedrooms and 7.5 bathrooms.

    The estate spans more than one flat acre and is one of only a handful of oceanfront Del Mar homes that includes a tennis court.

    Google Earth

    Durban has yet to confirm his ownership of the Del Mar compound, but he’s certainly no stranger to ultra-high-end real estate. Back in 2019, records reveal he and longtime wife Abby dropped $24 million to buy a brand-new mansion in prime Atherton, the small Silicon Valley town famously home to scores of the nation’s wealthiest tech executives. The couple also own a vacation home in California’s scenic Pebble Beach neighborhood worth approximately $10 million.

    The Durbans have also long maintained a seriously impressive blufftop mansion at the exclusive Kukio Golf and Beach Club on Hawaii’s Big Island, where one of their nearest neighbors is fellow billionaire Michael Dell—a longtime Durban business associate and the brash dealmaker’s ownership partner in the professional bull riding team Austin Gamblers. And astute soccer fans will know that Durban was also behind the $500 million purchase of a minority share in Manchester City, a landmark transfer inked in 2019. More

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    The Owners of Skechers Just Created a $31 Million SoCal Beach Compound

    The founding family of Skechers has officially added another piece to their ever-growing SoCal real estate portfolio. Records indicate an entity tied to the Manhattan Beach-based footwear brand has forked over $15.4 million in an off-market deal for the house immediately right next door to a Los Angeles-area parcel they already bought for $16 million back in spring 2019. Together, both properties span about three-quarters of an acre and cost a combined $31 million.

    The Greenbergs’ latest Hermosa Beach addition is a traditional three-bedroom, four-bath home with almost 2,800 square feet of single-level living space perched atop an attached two-car garage. Built back in the late 1940s but updated in the years since, and resting on a cul-de-sac parcel spanning a third of an acre, the tan wood-sided structure was most recently offered for rent at $14,750 per month.

    Though it was never officially on the market, a recent listing shows a glass-lined living room sporting a fireplace enhanced with a brick surround, as well as built-in shelving and doors spilling out to the backyard. Other highlights include a couple of dining areas, a kitchen outfitted with blue-and-white cabinetry and newer stainless appliances, and an adjacent den warmed by a Franklin stove and equipped with an integrated entertainment center.

    Elsewhere is a spacious primary bedroom suite with a fireplace, sitting area, walk-in closet, newly remodeled bath and access to a private patio; and outdoors, the tiered grounds overlook picturesque ocean vistas, and host an expansive terrace ideal for al fresco lounging and entertaining.

    Google Images

    As for the family’s other beach house, they acquired that place from former ballroom dancer/vitamin company founder Esmeralda Gallemore and her husband Ron almost five years ago. Built in 2015, the property rests on a third-acre hillside parcel of land spotlighted by a pool, sport court, fire-pit, seven-car subterranean garage and coastal vistas stretching from Palos Verdes to Malibu. Inside, five bedrooms and seven baths are spread across almost 7,300 square feet of multi-level living space featuring a living room anchored by a massive limestone fireplace and walls of glass, screening room and gym.

    Per Forbes, the Greenbergs are one of the nation’s richest families, with an estimated net worth of around $1.5 billion. More

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    A Historic French Villa That Once Hosted Grace Kelly Just Listed for $8.6 Million

    A French villa near Nice where Grace Kelly, the late Princess of Monaco, used to vacation is up grabs. However, this isn’t the first time that the palatial property has been on the market.  

    Dubbed Les Moulins du Villars, the Provence-Alpes Cote d’Azur residence was listed for a whopping $12.5 million back in August 2023. After failing to find a buyer, the estate is now back up for sale six months later at a discounted €7.95 million (or roughly $8.5 million) with Jack Harris of Knight Frank. The home itself, which was originally built way back in the 14th century as an olive oil and flour mill, has been completely transformed in the years since. The swanky spread was renovated in the ‘70s by Count Jean Fernand Joseph Gouin de Roumilly and entirely rebuilt over a decade ago in 2012. In 1980, Princess Grace was reported to have frequented the property with her daughter, Princess Caroline. The Hollywood starlet later died in a car accident in 1982. 

    A 14th-century olive oil mill in France that was converted into a lavish estate is back on the market.

    Knight Frank

    Located on the French Riveria in the village of Gilette, the digs measure 6,000 square feet and there are seven bedrooms split between the main dwelling and guest house. The roughly five-acre property also holds a slew of modern comforts too—though, you wouldn’t assume it based on its medieval surroundings. There’s an elevator, a tennis court that doubles as a helipad or soccer pitch, a wine cellar, and a fitness studio. At the same time, dotting the grounds are tons of citrus and olive trees, two vegetable gardens, a Koi pond, and a natural spring that, according to the listing, “is believed by locals to possess healing properties, historically making the mill a pilgrimage site and sanctuary for treating chronic ailments.” 

    The residence was a frequent hideaway for Grace Kelly, the late Princess of Monaco.

    Knight Frank

    Spanning four stories, the manse is made from local, indigenous stone and is decked out with original period furnishings and bespoke artwork. Another design detail is a glass-encased wrought iron wheel that was replaced in 2012. Inside, there’s essentially double of everything—two living rooms, two kitchens. However, there’s only one media room. Outside, the lot features several outbuildings, including a ruin that has been recently restored and a heated infinity pool that overlooks the picturesque Latti Valley. 

    Click here to see all the photos of Grace Kelly’s vacation villa. 

    Knight Frank


    Abby Montanez

    Abigail Montanez is a staff writer at Robb Report. She has worked in both print and digital publishing for over half a decade, covering everything from real estate, dining, travel and topics…

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